Chelation-controlled 1,3-asymmetric induction in the radical addition- allylation reactions of 4-hydroxy- and 4-alkoxy-2-methylenecarboxylic esters

Synlett

Volumn , Issue 7, 2000, Pages 1073-1075

  Nagano, Hajime ^a   Hirasawa, Tamano ^a   Yajima, Tomoko ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

1,3 asymmetric induction; Chelation control; Quaternary carbon center; Radical reaction

Indexed keywords

ALLYL COMPOUND; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CHELATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0033943764     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

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17. 3 of air were subsequently added. The reaction mixture was stirred at this temperature until the completion of the reaction (monitored by TLC; 1.5-10 h). After treatment with KF, the crude product was chromatographed on silica gel to yield the alkylation-allylation product.
18. 13C NMR and MS spectroscopic data together with high resolution mass spectral data.
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20. 2. The benzyl ether 2 gave 22 (syn) and 22 (anti) in 86% yield and in a ratio of 15: 1. The diastereoselectivity is superior to that of the methyl ether 1 (see Ref 3).
21. 2AlCl decomposed the starting material.
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